Cesium carbonate → HCID 57800507, compound

HRID 913656Notes

Reaction equation

HRID 913656 reaction equation
[CH2:1]([C:4]1[NH:5][C:6]2[C:11]([CH:12]=1)=[C:10]([C:13]([F:16])([F:15])[F:14])[C:9]([C:17]#[N:18])=[CH:8][CH:7]=2)[CH2:2][CH3:3].C([O-])([O-])=O.[Cs+].[Cs+].Cl[CH2:26][C:27]1[O:31][C:30]([C:32]([O:34]CC)=[O:33])=[CH:29][CH:28]=1>C(#N)C>[C:17]([C:9]1[C:10]([C:13]([F:15])([F:16])[F:14])=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]([CH2:26][C:27]1[O:31][C:30]([C:32]([OH:34])=[O:33])=[CH:29][CH:28]=1)[C:4]([CH2:1][CH2:2][CH3:3])=[CH:12]2)#[N:18]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 263166Ethyl 5-(chloromethyl)-2-furancarboxylateHCID 674051552-propyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile

Product 1

HCID 57800507HCID 57800507, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-propyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile (Example 153A) (0.500 g, 1.98 mmol) in anhydrous acetonitrile (25 mL) was added Cs2CO3 (6.50 g, 20.0 mmol) along with ethyl 5-(chloromethyl)-2-furancarboxylate (0.561 g, 3.00 mmol). The mixture was heated under N2, for 2 h. Upon cooling, the mixture was partitioned between EtOAc and water. The organic phase was separated, dried (MgSO4) and concentrated in vacuo. The residue was mixed with 1.0N LiOH (25 mL) and anhydrous 1,4-dioxane (2 5 mL) and the mixture was stirred at rt for 17 h. The mixture was diluted with water and extracted with Et2O. The organics were separated and the aqueous mixture was made acidic using 1.0N HCl. The aqueous mixture was extracted with EtOAc, dried (MgSO4) and concentrated to dryness to give a crude solid (0.579 g, 78%). This solid was used without further purification.

Workup

  1. temperatureThe mixture was heated under N2, for 2 h
  2. temperatureUpon cooling
  3. customthe mixture was partitioned between EtOAc and water
  4. customThe organic phase was separated
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. additionThe residue was mixed with 1.0N LiOH (25 mL) and anhydrous 1,4-dioxane (2 5 mL)
  8. additionThe mixture was diluted with water
  9. extractionextracted with Et2O
  10. customThe organics were separated
  11. extractionThe aqueous mixture was extracted with EtOAc
  12. dry with materialdried (MgSO4)
  13. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-9ef0ca7428704848a4aab4b3d6156195
Source dataset
uspto-grants-2011_09
Patent number
US08026262B2

Reaction notes

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